Nitromethane → HCID 66692726, compound

HRID 2368010Notes

Reaction equation

HRID 2368010 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:14]([B:22]2[O:26][C:25]([CH3:28])(C)C(C)(C)[O:23]2)=[C:15]([CH:18]=[CH:19][C:20]=1[F:21])C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:31](C)([O-:33])=[O:32].[OH-].[Na+].C1COCC1>O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:14]2[B:22]([OH:23])[O:26][CH:25]([CH2:28][N+:31]([O-:33])=[O:32])[C:15]=2[CH:18]=[CH:19][C:20]=1[F:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86664744HCID 86664744, compound

Product 1

HCID 66692726HCID 66692726, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Synthesized according to the methods of general procedure 8 in U.S. Pat. Pub. No. 20090227541 (U.S. patent application Ser. No. 12/142,692) using the following reactants and amounts: 3-(3-benzyloxy-propoxy)-4-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (0.40 g, 0.966 mmol), nitromethane (0.15 mL, 2.89 mmol), NaOH (0.038 g, 0.96 mmol), THF (10 mL), water (10 mL). This generated 0.34 g (94% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.83 (s, 1H), 7.32-7.02 (m, 7H), 5.78-5.75 (m, 1H), 5.28-5.23 (m, 1H), 4.60-4.56 (m, 1H), 4.42 (s, 2H), 4.37 (brs, 2H), 3.57 (brs, 2H), 1.92 (brs, 2H). 19F NMR (376 MHz, DMSO-d6 with D2O) δ (ppm): −132.3 (1F).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-e7ede47a002b469ebc600ab565943a55
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

Loading…